StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Citric Acid → tert-butyl 4-(6-bromo-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate

HRID 1476617
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1476617
[Br:1][C:2]1[S:6][C:5]([C:7]([O:9]C)=O)=[C:4]([NH:11][C:12]([NH:14][CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)=[O:13])[CH:3]=1.C[O-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[Br:1][C:2]1[S:6][C:5]2[C:7](=[O:9])[N:14]([CH:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)[C:12](=[O:13])[NH:11][C:4]=2[CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 311Citric AcidHCID 10942334Sodium MethoxideHCID 67258128Tert-butyl 4-(3-(5-bromo-2-(methoxycarbonyl)thiophen-3-yl)ureido)piperidine-1-carboxylate

Produkt 1

HCID 67258027tert-butyl 4-(6-bromo-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 4-({[5-bromo-2-(methoxycarbonyl)thiophen-3-yl]carbamoyl}amino)piperidine-1-carboxylate (37.6 g; compound B54a) in dry MeOH (205 ml) under argon atmosphere is added sodium methoxide (6.16 g) at RT. The reaction mixture is refluxed for 3 h, allowed to cool to RT and then poured into a solution of citric acid (21.9 g) in ice cold water (961 ml). The precipitated solid is filtered off, washed with ice cold water and dried in vacuo. The residue is taken up in MeOH (205 ml) and the resulting suspension is refluxed for 1 h. After cooling to RT all solids are filtered off, washed with MeOH and dried in vacuo to afford the title compound as a solid.

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for 3 h
  2. filtrationThe precipitated solid is filtered off
  3. washwashed with ice cold water
  4. customdried in vacuo
  5. temperaturethe resulting suspension is refluxed for 1 h
  6. temperatureAfter cooling to RT all solids
  7. filtrationare filtered off
  8. washwashed with MeOH
  9. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d3dcc09828494d2f8228a316d46432ed
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09018175B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion